US4471131AExpiredUtilityPatentIndex 63
Novel silyl esters of N-phosphonomethylglycine
Est. expirySep 27, 2003(expired)· nominal 20-yr term from priority
Inventors:FRANZ JOHN E
C07F 9/409A01N 57/20A01N 57/22C07F 9/4006C07F 9/3808
63
PatentIndex Score
4
Cited by
10
References
67
Claims
Abstract
This disclosure relates to novel silyl esters of N-phosphonomethylglycine useful as post-emergence herbicides.
Claims
exact text as granted — not AI-modifiedI claim:
1. A compound represented by the structure ##STR5## wherein R 1 and R 2 are independently selected from hydrogen, aryl, benzyl, substituted aryl and substituted benzyl groups, and X wherein X is ##STR6## wherein R 5 and R 6 are independently selected from alkyl groups having from 1 to 4 carbon atoms, phenyl and phenyl substituted with from 1 to 3 substituents selected from halogen, lower alkyl lower alkoxy, trifluoromethyl, nitro and cyano and R 7 is a tertiary alkyl group having from 4 to 7 carbon atoms, R 3 is hydrogen or a herbicidally non-interfering group, and R 4 is selected from hydrogen, X, alkyl groups having from 1 to 8 carbon atoms, naphthyl, phenyl and phenyl substituted with from 1 to 3 substituents selected from halogen, lower alkyl lower alkoxy, nitro, trifluoromethyl, and cyano provided that at least one of R 1 , R 2 , and R 4 is X.
2. A compound of claim 1 wherein R 3 is hydrogen.
3. A compound of claim 1 wherein R 4 is alkyl.
4. A compound of claim 1 wherein R 1 , R 2 , and R 4 are X.
5. A compound of claim 4 wherein R 3 is hydrogen.
6. A compound of claim 4 wherein R 7 is 1,1-dimethylethyl.
7. A compound of claim 1 wherein R 1 is X and R 2 and R 3 are hydrogen.
8. A compound of claim 1 wherein R 1 and R 2 are X and R 3 and R 4 are hydrogen.
9. A compound of claim 1 wherein R 5 and R 6 are alkyl and R 7 is 1,1-dimethylethyl.
10. A compound of claim 1 wherein R 5 and R 6 are phenyl or phenyl substituted with from 1 to 3 substituents selected from halogen, lower alkyl lower alkoxy, nitro and cyano.
11. A compound of claim 9 wherein R 5 and R 6 are methyl.
12. A compound of claim 1 wherein R 1 and R 2 are X, R 3 is hydrogen, and R 4 is lower alkoxy lower alkyl.
13. A compound of claim 7 wherein R 4 is hydrogen, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
14. A compound of claim 7 wherein R 4 is alkyl.
15. A compound of claim 14 wherein R 4 is n-butyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
16. A compound of claim 7 wherein R 4 is n-butyl, R 5 and R 6 are methyl, and R 7 is 1,1-dimethylethyl.
17. A compound of claim 7 wherein R 4 is haloalkyl.
18. A compound of claim 17 wherein R 4 is 2-chloroethyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
19. A compound of claim 4 wherein R 3 is hydrogen, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
20. A compound of claim 1 wherein R 1 and R 2 are X.
21. A compound of claim 20 wherein R 3 is hydrogen and R 4 is alkyl.
22. A compound of claim 21 wherein R 4 is methylethyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
23. A herbicidal composition which comprises an inert adjuvant and a herbicidally affective amount of a compound of the formula ##STR7## wherein R 1 and R 2 are independently selected from hydrogen, aryl, benzyl substituted aryl and substituted benzyl, and X wherein X is ##STR8## wherein R 5 and R 6 are independently selected from alkyl groups having from 1 to 4 carbon atoms, phenyl and phenyl substituted with from 1 to 3 substituents selected from halogen, lower alkyl lower alkoxy, --CF 3 , nitro and cyano and R 7 is a tertiary alkyl group having from 4 to 7 carbon atoms, R 3 is hydrogen or a herbicidally non-interfering group, and R 4 is selected from hydrogen, X, alkyl groups having from 1 to 8 carbon atoms, naphthyl, phenyl and phenyl substituted with from 1 to 3 substituents selected from halogen, lower alkyl lower alkoxy, nitro, trifluoromethyl, and cyano provided that at least one of R 1 , R 2 , and R 4 is X.
24. A herbicidal composition of claim 23 wherein R 3 is hydrogen.
25. A herbicidal composition of claim 23 wherein R 4 is alkyl.
26. A herbicidal composition of claim 23 wherein R 1 , R 2 , R 4 are X.
27. A herbicidal composition of claim 26 wherein R 3 is hydrogen.
28. A herbicidal composition of claim 26 wherein R 7 is 1,1-dimethylethyl.
29. A herbicidal composition of claim 23 wherein R 1 is X and R 2 and R 3 are hydrogen.
30. A herbicidal composition of claim 23 wherein R 1 and R 2 are X and R 3 and R 4 are hydrogen.
31. A herbicidal composition of claim 23 wherein R 5 and R 6 are alkyl and R 7 is 1,1-dimethylethyl.
32. A herbicidal composition of claim 23 wherein R 5 and R 6 are phenyl or phenyl substituted with from 1 to 3 substituents selected from halogen, lower alkyl- loweralkoxy, nitro and cyano.
33. A herbicidal composition of claim 31 wherein R 5 and R 6 are methyl.
34. A herbicidal composition of claim 23 wherein R 1 and R 2 are X, R 3 is hydrogen, and R 4 is lower alkoxy, lower alkyl.
35. A herbicidal composition of claim 29 wherein R 4 is hydrogen, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
36. A herbicidal composition of claim 29 wherein R 4 is alkyl.
37. A herbicidal composition of claim 36 wherein R 4 is n-butyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
38. A herbicidal composition of claim 29 wherein R 4 is n-butyl, R 5 and R 6 are methyl, and R 7 is 1,1-dimethylethyl.
39. A herbicidal composition of claim 29 wherein R 4 is haloalkyl.
40. A herbicidal composition of claim 39 wherein R 4 is 2-chloroethyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
41. A herbicidal composition of claim 26 wherein R 3 is hydrogen, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
42. A herbicidal composition of claim 23 wherein R 1 and R 2 are X.
43. A herbicidal composition of claim 42 wherein R 3 is hydrogen and R 4 is alkyl.
44. A herbicidal composition of claim 43 wherein R 4 is methylethyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
45. A method which comprises contacting a plant with a herbicidally effective amount of a compound of claim 1.
46. A method of claim 45 wherein R 3 is hydrogen.
47. A method of claim 45 wherein R 4 is alkyl.
48. A method of claim 45 wherein R 1 , R 2 , and R 4 are X.
49. A method of claim 48 wherein R 3 is hydrogen.
50. A method of claim 48 wherein R 7 is 1,1-dimethylethyl.
51. A method of claim 45 wherein R 1 is X and R 2 and R 3 are hydrogen.
52. A method of claim 45 wherein R 1 and R 2 are X and R 3 and R 4 are hydrogen.
53. A method of claim 45 wherein R 5 and R 6 are alkyl and R 7 is 1,1-dimethylethyl.
54. A method of claim 45 wherein R 5 and R 6 are phenyl or phenyl substituted with from 1 to 3 substituents selected from halogen, lower alkylloweralkoxy, nitro and cyano.
55. A method of claim 53 wherein R 5 and R 6 are methyl.
56. A method of claim 45 wherein R 1 and R 2 are X, R 3 is hydrogen, and R 4 is lower alkoxy, lower alkyl.
57. A method of claim 51 wherein R 4 is hydrogen, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
58. A method of claim 51 wherein R 4 is alkyl.
59. A method of claim 58 wherein R 4 is n-butyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
60. A method of claim 51 wherein R 4 is n-butyl, R 5 and R 6 are methyl, and R 7 is 1,1-dimethylethyl.
61. A method of claim 51 wherein R 4 is haloalkyl.
62. A method of claim 61 wherein R 4 is 2-chloroethyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
63. A method of claim 48 wherein R 3 is hydrogen, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
64. A method of claim 45 wherein R 1 and R 2 are X.
65. A method of claim 64 wherein R 3 is hydrogen and R 4 is alkyl.
66. A method of claim 65 wherein R 4 is methylethyl, R 5 and R 6 are phenyl, and R 7 is 1,1-dimethylethyl.
67. A compound of claim 1 wherein R 5 and R 6 are trifluoromethyl.Cited by (0)
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